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$143+ Cheap flights from Calgary (YYC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Calgary to Midway

Cheapest flights from Calgary to Midway
Explore the most affordable flight options available from Calgary to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:30 am
YYC
-
MDW
2 stops10h 07m
Delta
Tue 3/39:34 am
MDW
-
YYC
2 stops12h 20m
Delta
Deal found 1/25$231
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:30 am
YYC
-
MDW
1 stop5h 55m
Delta
Wed 3/189:30 am
MDW
-
YYC
2 stops10h 42m
Delta
Deal found 1/25$302
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:30 am
YYC
-
MDW
1 stop5h 35m
Delta
Wed 3/410:49 am
MDW
-
YYC
1 stop9h 20m
Delta
Deal found 1/25$304
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/46:30 am
YYC
-
MDW
1 stop5h 36m
Delta
Wed 2/119:33 am
MDW
-
YYC
2 stops12h 21m
Delta
Deal found 1/25$305
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:30 am
YYC
-
MDW
1 stop5h 35m
Delta
Thu 3/59:34 am
MDW
-
YYC
2 stops12h 24m
Delta
Deal found 1/25$312
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:30 am
YYC
-
MDW
1 stop5h 35m
Delta
Sun 3/89:35 am
MDW
-
YYC
2 stops10h 53m
Delta
Deal found 1/25$313
This Kiwi.com deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:30 am
YYC
-
MDW
2 stops12h 30m
Multiple Airlines
Mon 2/2311:05 am
MDW
-
YYC
1 stop14h 00m
Multiple Airlines
Deal found 1/25$322
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:30 am
YYC
-
MDW
1 stop5h 35m
Delta
Sun 3/89:35 am
MDW
-
YYC
2 stops12h 23m
Delta
Deal found 1/25$325
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:30 am
YYC
-
MDW
2 stops10h 07m
Delta
Mon 2/239:50 am
MDW
-
YYC
2 stops10h 22m
Delta
Deal found 1/25$327
This Delta deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:30 am
YYC
-
MDW
1 stop8h 24m
Delta
Sun 3/89:35 am
MDW
-
YYC
2 stops12h 23m
Delta
Deal found 1/24$331
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:15 am
YYC
-
MDW
2 stops11h 31m
Delta
Fri 3/69:50 am
MDW
-
YYC
2 stops10h 22m
Delta
Deal found 1/25$332

Find flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$231
(Delta)

One-way from

$143
(Delta)

Popular in

July

Cheapest in

April

Average price

$234
Provider with most accurate pricing for Calgary-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Calgary-Chicago Midway flights.
Search Deals
From Calgary to Chicago Midway
Search Deals
One-way flight from Calgary to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 2/27

6:30 am-5:37 pm

2 stops10h 07m

Chicago Midway

Tue 3/3

1:49 pm-8:54 pm

1 stop8h 05m

$231

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 3/11

6:30 am-1:25 pm

1 stop5h 55m

Chicago Midway

Wed 3/18

9:30 am-7:12 pm

2 stops10h 42m

$302

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 2/26

6:30 am-1:05 pm

1 stop5h 35m

Chicago Midway

Wed 3/4

10:49 am-7:09 pm

1 stop9h 20m

$304

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 2/24

6:30 am-5:37 pm

2 stops10h 07m

Chicago Midway

Mon 3/2

9:50 am-7:12 pm

2 stops10h 22m

$304

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 2/26

6:30 am-1:05 pm

1 stop5h 35m

Chicago Midway

Mon 3/2

9:50 am-11:05 pm

2 stops14h 15m

$304

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/7

6:30 am-4:16 pm

1 stop8h 46m

Chicago Midway

Tue 2/10

1:51 pm-8:54 pm

1 stop8h 03m

$305

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 2/6

6:30 am-1:06 pm

1 stop5h 36m

Chicago Midway

Sat 2/14

11:45 am-11:05 pm

2 stops12h 20m

$305

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 2/6

6:30 am-1:06 pm

1 stop5h 36m

Chicago Midway

Mon 2/9

9:53 am-11:02 pm

2 stops14h 09m

$305

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/7

6:30 am-4:16 pm

1 stop8h 46m

Chicago Midway

Mon 2/9

9:53 am-11:02 pm

2 stops14h 09m

$305

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 2/6

6:30 am-1:06 pm

1 stop5h 36m

Chicago Midway

Tue 2/10

1:51 pm-8:54 pm

1 stop8h 03m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 21 results
1
2
3
  • Most accurate provider: When it comes to deals on Calgary-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Calgary-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Calgary-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Calgary-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Calgary-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    For a flight from Calgary to Chicago Midway, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Calgary on a regular basis.

  • How long is the flight from Calgary to Chicago Midway Airport?

    A quick flight from Calgary to Chicago Midway Airport can take about 10h 07m. Delta provides one of the quickest options available for as low as $231. Calgary and Chicago Midway Airport are separated by a distance of 1396 mi.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Calgary to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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